So, here's the thing about Josy (preemptive apology to
ChipLecsap if this offends), but she doesn't seem to have any kind of baggage at all that would give her any kind of engaging personal story. I say this as someone who likes Josy because I like her personality, she's hot, and I get to have her and Maya at the same time (win-win), but she currently lacks any kind of personal or emotional problem that would give her an interesting character arc.
With Maya, we all know what her problems are.
With Sage, there's the Chad situation/betrayal/who-knows-what that's going on there plus she's the President of the HOTs and if Quinn's dealings ever come to light, that'll bring Sage's down with it.
With Bella, we have whatever's going with her and James and her being very emotionally guarded and closed off which may or may not be related to the James situation.
With Jill, we have the whole the Tybalt blackmail BS, but there may also be family issues too since she seems to somewhat resent her legacy and fortune, plus she may be dealing with some things related to her sister.
With Josy, everything is...well...pretty OK for her personally. The only personal issues seems to be with Tommy, Monica, and her Mom, but those are very minor. The only major problem in her life is Maya's Dad impeding their relationship, but that could be resolved if she just dumped Maya and got out of that relationship. So really, she doesn't have much going for her in terms of any major personal drama, and that might sound quite good to some, but in the context of this game, it seems like it could be quite boring and basic if she gets a solo path unless some major drama is injected into her personal life.